CN111220586A - Preparation method of fluorescent probe test paper for detecting lead content in soil - Google Patents
Preparation method of fluorescent probe test paper for detecting lead content in soil Download PDFInfo
- Publication number
- CN111220586A CN111220586A CN202010098283.3A CN202010098283A CN111220586A CN 111220586 A CN111220586 A CN 111220586A CN 202010098283 A CN202010098283 A CN 202010098283A CN 111220586 A CN111220586 A CN 111220586A
- Authority
- CN
- China
- Prior art keywords
- test paper
- fluorescent probe
- probe test
- detecting
- fluorescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/24—Earth materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6443—Fluorimetric titration
Abstract
The invention relates to a method for preparing fluorescent probe test paper for detecting lead content in soil, which comprises an organic micromolecular fluorescent material shown as a formula (I); the fluorescent probe test paper is distinguished obviously under different heavy metal lead ion concentrations, can semi-quantitatively detect lead ions in sewage, cosmetics, food and the like, and has substantial significance; the fluorescent probe test paper for detecting heavy metal lead ions has the advantages of simple preparation, low detection limit, sensitive reaction, high efficiency and the like.
Description
Technical Field
The invention relates to a preparation method of fluorescent probe test paper for detecting lead content in soil, belonging to the field of soil detection.
Background
Lead is common in mineral products, the combustion of coal and petroleum and the exploitation of mines are the main ways of bringing lead pollution, and in addition, pesticides, herbicides, batteries, pigments, dyes, electroplating, pipes and the like also bring lead pollution. About 40 million tons of lead are discharged into the environment in various ways every year worldwide, causing irreversible pollution to the environment. The soil has strong adsorption effect on lead, the lead desorbed from the air or the lead carried by fertilizer, excrement and sludge is easily adsorbed on the soil surface and a plough layer by the soil, the lead pollution of the soil indirectly causes pollution to plants, and the vegetables are an effective way for enriching the lead in the soil to a human body through a food chain. Excessive lead intake by human body can not only inhibit the synthesis process of heme, leading to the reduction of hemoglobin in erythrocytes to cause anemia, but also cause damage to the central nervous system and peripheral nerves, and under the condition of mild poisoning, symptoms such as headache, dizziness, insomnia, hypomnesis and the like can appear. Lead causes irreversible damage to the mental-intelligence-behavior development of children, and lead damages the nervous system to cause hyperlocomotion, short attention and mental retardation of children. Under the condition of acute lead poisoning or long-term excessive lead absorption, renal tubular injury can be caused, the content of amino acid, glucose and phosphate in the urine towel is increased, and the Vanconi disease is generated. Although only 5-10% of lead is absorbed by human body after entering human body with food, long-term intake of lead can cause lead accumulation in human body. A large number of childhood lead poisoning events occur each year. Lead can play a role in quickly whitening with copper atoms in the aminase in a human body, so that a large amount of lead ions are added into cosmetics by bad merchants to play a role in quickly whitening.
The traditional detection of heavy metal ions mainly uses an electrochemical method, but the electrochemical method can only detect total heavy metal ions and can not accurately measure single heavy metal lead ions. The test paper method is characterized in that certain specific color developing agents are attached to the test paper, the color of the test paper is changed after the color developing agents are contacted with heavy metal ions, and the type and the content of the heavy metals can be analyzed by comparing the color developing agents with a colorimetric plate through naked eyes. The common test paper method has the advantages of convenience, low price, high analysis speed, simple operation, suitability for field detection and the like, is mainly used for qualitative heavy metal detection at present, and cannot perform semi-quantitative detection; however, the research and development of the fluorescent probe test paper specially used for detecting heavy metal cadmium ions still basically belong to a blank state at present.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of fluorescent probe test paper for detecting the lead content of soil. The organic small-molecule fluorescent probe test paper has the advantages of simple manufacture, low detection limit, sensitive reaction, high efficiency and the like, and solves the defects of insufficient detection precision and higher detection limit of a test paper method on the market. The organic small molecule fluorescent probe test paper also has the characteristic of wide application range, can detect heavy metal lead ions only by a small handheld fluorescent detector, can distinguish the content range of the heavy metal lead ions according to the fluorescence intensity detected by the handheld fluorescent detector, and has wide application prospect.
The synthetic route of the heavy metal lead ion organic micromolecule fluorescent probe provided by the invention is as follows:
the specific reaction steps are as follows:
(1) dissolving 8-hydroxyquinoline and hexamethylenetetramine in a methanol solvent according to a molar ratio of 1:2, carrying out reflux reaction for 2 hours at 70 ℃, cooling, carrying out reduced pressure rotary evaporation, and purifying by a chromatographic column to obtain the 5, 7-dialdehyde-8-hydroxyquinoline.
(2) Dissolving 3-iodopropane-1-ammonia and 2-methylbenzothiazole in n-butanol according to a molar ratio of 3:1, reacting for 2-6h at 60 ℃ by using a sealed high-pressure bottle to obtain yellow solid 3- (3-aminopropyl) -2-methylbenzothiazole, filtering, washing twice by using 1 equivalent of diethyl ether, and drying to obtain the product with the yield of over 98%.
(3) Reacting 5, 7-dialdehyde-8-hydroxyquinoline with twice amount of 3- (3-aminopropyl) -2-methylbenzothiazole in a normal butanol system, adding organic base triethylamine as a condensation catalyst, reacting for 2-6h at 120 ℃, wherein when the system begins to condense, the reaction system is colorless and turns into red, and finally, a black solid is separated out from the reaction system, wherein the solid is an organic small-molecular fluorescent compound (I), and then carrying out suction filtration and drying.
The preparation method of the fluorescent test paper provided by the invention specifically comprises the following operations:
and soaking the blank test paper in an acetone dispersion solution of the organic small-molecule fluorescent compound material, taking out the test paper after soaking for a period of time, placing the test paper in a clean and ventilated place, and naturally drying the test paper to finally obtain the fluorescent probe test paper for detecting the heavy metal lead ions.
Further, the blank test paper is soaked in an acetone dispersion solution of the organic small-molecule fluorescent compound for 8-15 minutes.
A method for detecting heavy metal lead ions by using the fluorescent probe test paper comprises the following specific operations:
taking a piece of fluorescent probe test paper, dissolving a liquid to be detected by using an acetone solution, immersing the test paper in the acetone solution, and taking out the test paper after 2-5 minutes; and (3) the test paper is placed under a fluorescent lamp for observation and comparison, and at the moment, the higher the content of heavy metal lead ions is, the stronger the fluorescence intensity is.
Has the advantages that: according to the heavy metal lead ion fluorescent probe test paper provided by the invention, an acetone solution of an organic small molecular fluorescent compound emits weak fluorescence under a fluorometer, a Tris-HCl solution containing heavy metal lead ions is gradually dripped into the acetone solution of the organic small molecular fluorescent compound, so that the fluorescence of a fluorescence spectrum is enhanced, and when the concentration of the organic small molecular fluorescent compound reaches 5 mu M, the intensity is about 25 times of the original intensity. Therefore, the fluorescent probe test paper provided by the invention has obvious phenomenon and high sensitivity when being used for detecting heavy metal lead ions. The heavy metal lead ion organic small molecule fluorescent probe test paper has the advantages of simple preparation, easy operation, easy carrying and good anti-interference performance, can achieve the purposes of naked eye identification and field inspection implementation, and has better application prospect.
Drawings
FIG. 1 is a fluorescence curve of organic small molecule fluorescent compound (I).
FIG. 2 is a graph of the titration of heavy metal lead ions in Tris-HCl by organic small molecule fluorescent compound (I).
FIG. 3 is a graph of the titration of heavy metal lead ions in acetone by organic small molecule fluorescent compound (I).
FIG. 4 is a comparison of fluorescent probe test paper at different concentrations of heavy metal lead ions.
FIG. 5 is a comparison of fluorescent probe strips in detecting lead ions in sewage.
Detailed description of the preferred embodiments
EXAMPLE 1 Synthesis of organic fluorescent Small molecules
(1) Dissolving 8-hydroxyquinoline and hexamethylenetetramine in a methanol solvent according to a molar ratio of 1:2, carrying out reflux reaction for 2 hours at 70 ℃, cooling, carrying out reduced pressure rotary evaporation, and purifying by a chromatographic column to obtain the 5, 7-dialdehyde-8-hydroxyquinoline.
(2) Dissolving 3-iodopropane-1-ammonia and 2-methylbenzothiazole in n-butanol according to a molar ratio of 3:1, reacting for 2-6h at 60 ℃ by using a sealed high-pressure bottle to obtain yellow solid 3- (3-aminopropyl) -2-methylbenzothiazole, filtering, washing twice by using 1 equivalent of diethyl ether, and drying to obtain the product with the yield of over 98%.
(3) Reacting 5, 7-dialdehyde-8-hydroxyquinoline with twice amount of 3- (3-aminopropyl) -2-methylbenzothiazole in a normal butanol system, adding organic base triethylamine as a condensation catalyst, reacting for 2-6h at 120 ℃, wherein when the system begins to condense, the reaction system is colorless and turns into red, and finally, a black solid is separated out from the reaction system, wherein the solid is an organic small-molecular fluorescent compound (I), and then carrying out suction filtration and drying.
Example 2 graph of titration of heavy metal lead ions by small organic molecule fluorescent compounds in Tris-HCl.
The stock solution of the small organic molecular fluorescent compound of the present invention, which is 5mM, is diluted to a concentration of 5 μ M, heavy metal lead ions of different concentrations are added, and the fluorescence intensities of the heavy metal lead ions are measured with a fluorescence spectrophotometer (slit width: 10, scanning speed: 200nm, Ex: 526nm), and the titration solution is Tris-HCl solution. After the organic small-molecule fluorescent compound is combined with the heavy metal lead ions, the fluorescence intensity is obviously enhanced along with the increase of the concentration of the metal, and the concentration is not enhanced when the concentration reaches saturation definitely, as shown in figure 2. While the fluorescence intensity of the organic small-molecule fluorescent compound is very weak when the organic small-molecule fluorescent compound is not combined with heavy metal lead ions, as shown in figure 1.
Example 3 graph of titration of heavy metal lead ions by small organic molecule fluorescent compounds in acetone.
The stock solution of the small organic molecular fluorescent compound of the present invention, which is 5mM, is diluted to a concentration of 5 μ M, heavy metal lead ions of different concentrations are added, and the fluorescence intensities of the heavy metal lead ions are measured with a fluorescence spectrophotometer (slit width: 10, scanning speed: 200nm, Ex: 526nm), and the titrated solution is acetone solution. After the organic small-molecule fluorescent compound is combined with the heavy metal lead ions, the fluorescence intensity is obviously enhanced along with the increase of the concentration of the metal, the concentration is not enhanced when the concentration reaches saturation, but the fluorescence intensity is about 40 percent lower than that of a Tris-HCl solution, as shown in figure 3.
Example 4 preparation of fluorescent probe paper for small organic molecule fluorescent compounds.
Soaking the blank test paper in an acetone dispersion solution of an organic small-molecule fluorescent compound material, wherein the concentration of the organic small-molecule fluorescent compound material is 100 mu M, taking out the test paper after soaking for a period of time, placing the test paper in a clean and ventilated place, and naturally drying the test paper to finally obtain the fluorescent probe test paper for detecting heavy metal lead ions. Further, the blank test paper is soaked in an acetone dispersion solution of the organic small-molecule fluorescent compound for 10-15 minutes. Thus obtaining the organic small molecular fluorescent compound fluorescent probe test paper.
Example 5 comparative images of fluorescence of fluorescent probe strips under different concentrations of heavy metal lead ions and the like.
5 parts of the fluorescent probe test paper prepared in example 4 were immersed in 0.01. mu.M, 0.1. mu.M, 1. mu.M, 10. mu.M and 100. mu.M solutions of heavy metal lead ions for 3 seconds, and the fluorescent intensity was observed under irradiation with a 15W 365nm portable ultraviolet lamp. The fluorescent probe can well distinguish heavy metal lead ion solutions with different concentrations. The results are shown in FIG. 4.
Example 6 application of fluorescent probe test paper to heavy metal lead ion content in sewage
Taking 5ml of sewage, filtering with a 0.25 mu m filter membrane, removing impurities of other insoluble substances in the sewage, reducing experimental interference, then averagely dividing the filtered sewage into 5 parts, and then respectively diluting by 1 time, 10 times, 100 times, 1000 times and 10000 times, and respectively numbering 1-5. The heavy metal lead ion fluorescent probe test paper is respectively soaked in No. 1-5 solution for 3s and respectively marked with the test paper 1 '-5' corresponding to the serial number of sewage 1-5, and then the soaked fluorescent probe test paper is dried in the shade under natural conditions or is dried in an oven. The fluorescence intensity was observed by irradiating with a portable ultraviolet lamp of 15W and 365nm, respectively. The fluorescent probe test paper 1 '-5' shows different fluorescence intensities under the irradiation of an ultraviolet lamp. As shown in FIG. 5, the test paper for the 1 '-5' fluorescent probe is arranged from left to right. The detection limit of the detection reaches two exponential detection of national heavy metal lead ion pollution discharge standard.
Claims (4)
1. A preparation method of fluorescent probe test paper for detecting lead content in soil is characterized by comprising the following steps: containing an organic small molecule fluorescent material;
the structural formula of the organic micromolecule fluorescent material is shown as (I):
wherein R is-CH3、-CH2CH3-OH; n and m are 0-5;
the organic small molecule fluorescent material (I) comprises the following specific reaction steps:
(1) dissolving 8-hydroxyquinoline and hexamethylenetetramine in a molar ratio of 1:2 in a methanol solvent, carrying out reflux reaction at 70 ℃ for 2 hours, cooling, carrying out reduced pressure rotary evaporation, and purifying by a chromatographic column to obtain 5, 7-dialdehyde-8-hydroxyquinoline;
(2) dissolving 3-iodopropane-1-ammonia and 2-methylbenzothiazole in n-butanol according to the molar ratio of 3:1, reacting for 2-6h at 60 ℃ by using a sealed high-pressure bottle to obtain yellow solid 3- (3-aminopropyl) -2-methylbenzothiazole, filtering, washing twice by using 1 equivalent of diethyl ether, and drying to obtain a product with the yield of more than 98%;
(3) reacting 5, 7-dialdehyde-8-hydroxyquinoline with twice amount of 3- (3-aminopropyl) -2-methylbenzothiazole in an n-butanol system, adding organic base triethylamine as a condensation catalyst, reacting for 2-6h at 120 ℃, wherein when the system begins to be condensed, the reaction system is colorless and turns into red, and finally, a black solid is separated out from the reaction system, wherein the solid is an organic small-molecule fluorescent compound (I), and then carrying out suction filtration and drying;
the preparation method of the fluorescent probe test paper comprises the steps of soaking blank test paper in acetone dispersion solution of a fluorescent material for 8-15 minutes, taking out the test paper, placing the test paper in a clean and ventilated place, and naturally drying the test paper in the air to finally obtain the fluorescent probe test paper for detecting heavy metal lead ions;
the concentration of the organic small-molecule fluorescent material is 0.05-1 mM.
2. The method for preparing the fluorescent probe test paper for detecting the lead content in the soil according to claim 1, which is characterized in that: the use method of the fluorescent probe test paper comprises the following steps: taking a piece of fluorescent probe test paper, dissolving a liquid to be detected by using an acetone solution, immersing the test paper in the acetone solution, and taking out the test paper after 2-5 minutes; the test paper is placed under a fluorescent lamp for observation and comparison, and the higher the content of heavy metal lead ions is, the stronger the fluorescence intensity is.
3. The fluorescent probe test paper for detecting the lead content in the soil according to claim 1, which is characterized in that: the organic small molecule fluorescent material is used for detecting the content of heavy metal lead ions.
4. The fluorescent probe strip for detecting lead content in soil according to claim 1 or 3, wherein: the fluorescent probe test paper can be used for semi-quantitatively detecting the content of lead ions in sewage, cosmetics and foods.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010098283.3A CN111220586A (en) | 2020-02-17 | 2020-02-17 | Preparation method of fluorescent probe test paper for detecting lead content in soil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010098283.3A CN111220586A (en) | 2020-02-17 | 2020-02-17 | Preparation method of fluorescent probe test paper for detecting lead content in soil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111220586A true CN111220586A (en) | 2020-06-02 |
Family
ID=70810951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010098283.3A Withdrawn CN111220586A (en) | 2020-02-17 | 2020-02-17 | Preparation method of fluorescent probe test paper for detecting lead content in soil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111220586A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253387A (en) * | 2020-02-17 | 2020-06-09 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting mercury content in sewage |
| CN111929284A (en) * | 2020-08-01 | 2020-11-13 | 淮南师范学院 | Rapid detection technology for lead ions in agricultural products |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134452A (en) * | 2018-09-05 | 2019-01-04 | 东华大学 | A kind of fluorescence probe and its preparation and application |
| CN111253387A (en) * | 2020-02-17 | 2020-06-09 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting mercury content in sewage |
-
2020
- 2020-02-17 CN CN202010098283.3A patent/CN111220586A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134452A (en) * | 2018-09-05 | 2019-01-04 | 东华大学 | A kind of fluorescence probe and its preparation and application |
| CN111253387A (en) * | 2020-02-17 | 2020-06-09 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting mercury content in sewage |
Non-Patent Citations (1)
| Title |
|---|
| 邢其毅 等: "《基础有机化学（第三版）下册》", 31 December 2008, 高等教育出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253387A (en) * | 2020-02-17 | 2020-06-09 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting mercury content in sewage |
| CN111929284A (en) * | 2020-08-01 | 2020-11-13 | 淮南师范学院 | Rapid detection technology for lead ions in agricultural products |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9175165B2 (en) | Chemosensors for hydrogen sulfide | |
| US8058075B2 (en) | Molecular fluorescence sensor for highly sensitive and selective detection of mercury | |
| CN111220586A (en) | Preparation method of fluorescent probe test paper for detecting lead content in soil | |
| Peng et al. | Coumarin–hemicyanine conjugates as novel reaction-based sensors for cyanide detection: convenient synthesis and ICT mechanism | |
| Kazemzadeh et al. | Determination of Hg2+ by diphenylcarbazone compound in polymer film | |
| CN104422686A (en) | Method for determining aflatoxin | |
| CN107607507B (en) | Fluorescence detection method for organophosphorus pesticide residues | |
| Zuo et al. | Ratiometric fluorescence sensing of formaldehyde in food samples based on bifunctional MOF | |
| CN111233856A (en) | Preparation method of fluorescent probe test paper for detecting chromium content in soil | |
| CN111303143A (en) | Preparation method of fluorescent probe test paper for detecting cadmium content in soil | |
| CN113087651A (en) | Compound containing indole group and preparation method and application thereof | |
| CN111253388A (en) | Preparation method of fluorescent probe test paper for detecting copper content in sewage | |
| CN113736091B (en) | Method for detecting quercetin by using fluorescent micrometer probe and application | |
| Zhang et al. | Capsulation of red emission chromophore into the CoZn ZIF as nanozymes for on-site visual cascade detection of phosphate ions, o-phenylenediamine, and benzaldehyde | |
| CN113563353B (en) | For Hg in aqueous solution2+Bifunctional fluorescent probe for real-time pH detection | |
| CN113563592B (en) | Fluorescent microsphere, fluorescent probe and method for detecting tetracycline | |
| CN111253387A (en) | Preparation method of fluorescent probe test paper for detecting mercury content in sewage | |
| CN107501271A (en) | A kind of sensor molecule of colorimetric fluorescence binary channels identification mercury ion and its synthesis and application | |
| CN110317175B (en) | Naphthalene derivative and synthesis method and application thereof | |
| CN108760707B (en) | Application of probe reagent | |
| CN112094299B (en) | Metal iridium complex and preparation method and application thereof | |
| CN112250674B (en) | 2, 3-diaminophenazine derivative and synthesis method and application thereof | |
| CN115160209B (en) | Indole group-containing compound and preparation method and application thereof | |
| Shinde et al. | Facile green synthesized C-4-Hydroxy-3-methoxyphenylcalix [4] Resorcinarene (CHMPCR) for photometric sensing of Fe3+ and Cu2+ ions | |
| CN108774241B (en) | Probe and preparation and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20200602 |
|
| WW01 | Invention patent application withdrawn after publication |